Hydrochloric Acid → HCID 89677031, compound

HRID 2278245Notes

Reaction equation

HRID 2278245 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.CO.[OH-].[Li+].Cl>O>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][N:13]([CH2:12][C:3]2[CH:4]=[CH:5][C:6]([C:8]([OH:10])=[O:9])=[CH:7][C:2]=2[Cl:1])[CH2:14][CH2:15]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 89676966HCID 89676966, compound

Product 1

HCID 89677031HCID 89677031, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL round-bottom flask was charged with tert-butyl 4-[[2-chloro-4-(methoxycarbonyl)phenyl]methyl]piperazine-1-carboxylate (3.54 g, 9.60 mmol, 1.00 equiv), methanol (20 mL), H2O (10 mL), lithium hydroxide (0.690 g, 28.8 mmol, 3.00 equiv). The resulting solution was stirred overnight at room temperature. The pH value of the solution was adjusted to 6 with hydrogen chloride (1 mol/L). The resulting solution was extracted with dichloromethane (3×20 mL) and the organic layers were combined, washed with brine (1×20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to provide 2.90 g (crude) of 4-([4-[(tert-butoxy)carbonyl]piperazin-1-yl]methyl)-3-chlorobenzoic acid as a white solid. 1H NMR 300 MHz (CDCl3) δ 7.89-8.06 (m, 3H), 3.88 (s, 2H), 3.56 (br, 4H), 2.68 (br, 4H), 1.46 (s, 9H). LCMS (ESI, m/z): 355 [M+H]+.

Workup

  1. extractionThe resulting solution was extracted with dichloromethane (3×20 mL)
  2. washwashed with brine (1×20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7539bd55f3e64c80a5f6d3a0cbf26bbf
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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